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4954

Sigma-Aldrich

Oleic Acid

Synonym(s):

Oleic Acid, cis-9-Octadecenoic Acid, 18:1

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About This Item

Empirical Formula (Hill Notation):
C18H34O2
CAS Number:
112-80-1
Molecular Weight:
282.46
MDL number:
MFCD00064242
UNSPSC Code:
12352211
NACRES:
NA.77

Assay

≥99% (GC)

Quality Level

100

form

liquid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze

color

colorless

solubility

chloroform: 10 mg/mL
ethanol: 5 mg/mL

density

0.89 g/mL

shipped in

ambient

storage temp.

2-8°C

InChI

1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9+

InChI key

ZQPPMHVWECSIRJ-MDZDMXLPSA-N

General description

A cis-unsaturated fatty acid that has been shown to activate protein kinase C in hepatocytes. Potentiates acetylcholine receptor currents by activating CaM kinase II, independent of the PKC pathway.
Unsaturated fatty acid that has been shown to activate protein kinase C in hepatocytes. Density: 0.89 g/ml.

Biochem/physiol Actions

Cell permeable: no
Product does not compete with ATP.
Reversible: no

Packaging

Packaged under inert gas

Warning

Toxicity: Standard Handling (A)

Other Notes

Nishizaki, T., et al. 1997. NeuroReport 8, 597.
Bessesen, D.H., et al. 1993. J. Lipid Res.34, 229.
Felden, F., et al. 1993. Biochem. Biophys. Res. Commun.190, 602.
Williams, L.L., et al. 1993. Proc. Soc. Exp. Biol. Med.202, 239.
Diaz-Guerra, M.J. 1991. J. Biol. Chem.266, 23568.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

4954-1GM:
4954-GM:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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M J Díaz-Guerra et al.
The Journal of biological chemistry, 266(35), 23568-23576 (1991-12-15)
The effect of oleate on the subcellular distribution of protein kinase C (PKC) was studied in isolated hepatocytes and in perfused rat liver in the presence of physiological concentrations of serum albumin. A time- and dose-dependent translocation of PKC from
F Felden et al.
Biochemical and biophysical research communications, 190(2), 602-608 (1993-01-29)
The free fatty acid (FFA) concentration in the epididymal cytosol of the adult rat was found to be 20-fold higher than in the serum. The binding of [3H] dihydrotestosterone to epididymal rat androgen binding protein (rABP) was modified by physiological
L L Williams et al.
Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.), 202(2), 239-245 (1993-02-01)
The polyunsaturated omega-6 fatty acid, arachidonic acid ([AA] 20:4n-6), is both the key of the immunoregulatory substances, prostaglandins, and leukotrienes, and an essential component of immune cell membrane phospholipids, providing stability and flexibility to ensure cellular function. To explore possible
T Nishizaki et al.
Neuroreport, 8(3), 597-601 (1997-02-10)
Oleic acid, a cis-unsaturated free fatty acid, is proposed to be involved in the protein kinase C (PKC) activation pathway. Its biological actions, however, have not been well-characterized. We examined the effects of oleic acid on acetylcholine (ACh)-gated channel currents
D H Bessesen et al.
Journal of lipid research, 34(2), 229-238 (1993-02-01)
Lipoprotein lipase (LPL) is important for the delivery of triglyceride fatty acids (TGFA) to a variety of tissues. We have used measurements of heparin-releasable LPL activity, immunohistochemistry, in situ hybridization, and Northern analysis to more fully characterize the location of

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